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The mixed organic–inorganic title salt, C7H18N2O2+·C2HO4·Cl, forms an assembly of ionic components which are stabilized through a series of hydrogen bonds and charge-assisted inter­molecular inter­actions. The title assembly crystallizes in the monoclinic C2/c space group with Z = 8. The asymmetric unit consists of a 4-(3-aza­niumylprop­yl)mor­pho­lin-4-ium dication, a hydrogen oxalate counter-anion and an inorganic chloride counter-anion. The organic cations and anions are connected through a network of N—H...O, O—H...O and C—H...O hydrogen bonds, forming several inter­molecular rings that can be described by the graph-set notations R33(13), R21(5), R12(5), R21(6), R23(6), R22(8) and R33(9). The 4-(3-aza­niumylprop­yl)morpholin-4-ium dications are inter­connected through N—H...O hydrogen bonds, forming C(9) chains that run diagonally along the ab face. Furthermore, the hydrogen oxalate anions are inter­connected via O—H...O hydrogen bonds, forming head-to-tail C(5) chains along the crystallographic b axis. The two types of chains are linked through additional N—H...O and O—H...O hydrogen bonds, and the hydrogen oxalate chains are sandwiched by the 4-(3-aza­niumylprop­yl)morpholin-4-ium chains, forming organic layers that are separated by the chloride anions. Finally, the layered three-dimensional structure is stabilized via inter­molecular N—H...Cl and C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614022232/fm3027sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614022232/fm3027Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614022232/fm3027Isup3.cml
Supplementary material

CCDC reference: 1028136

Introduction top

As part of our continued inter­est in the multicomponent synthesis of compounds with the pyrrolidinedione skeleton, some of which have reportedly demonstrated promising anti­microbial properties (Gein et al., 2007), we report here the structure of 4-(3-aza­niumyl­propyl)­morpholin-4-ium chloride hydrogen oxalate, (I), an organic–inorganic mixed salt formed as a by-product during the synthesis of the hydro­chloride salt of the pyrrolidinone carbaldehyde parent compound, 4-(benzo­furan-2-carbonyl)-5-[4-(tert-butyl)­phenyl]-3-hy­droxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one, (II). Mixed salts have many practical and potential applications in the fields of magnetism and electric conductors, energy storage, solar energy conversion, as well as catalysis and the biomedical field (Hill & Prossner-McCartha, 1995; Mizuno & Misomo, 1998; Gouzerh & Proust, 1998; Proust et al., 1993; Zhuang et al., 2010; Huang et al., 2009; Zhou & Yu, 2012; You et al., 2006). The crystal packing of such compounds is often characterized by extensive hydrogen bonding and charge-assisted inter­molecular inter­actions (Brammer et al., 2002; Huang et al., 2009).

Experimental top

Synthesis and crystallization top

Methyl (2Z)-4-(1-benzo­furan-2-yl)-2-hy­droxy-4-oxobut-2-enoate (0.200 g, 0.816 mmol) was dissolved in 1,4-dioxane (5 ml). One molar equivalent of 4-(3-amino­propyl)­morpholine (0.816 mmol, 0.119 ml) was added to the dioxane mixture, resulting in a yellow precipitate forming upon addition. One molar equivalent of tert-butyl­benzaldehyde (0.816 mmol, 0.137 ml) was added to the mixture and stirred at room temperature for 5 min. 4-(Benzo­furan-2-carbonyl)-5-[4-(tert-butyl)­phenyl]-3-hy­droxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one was isolated as a yellow powder (0.579 mmol, 0.291 g; 71% yield) and dried in vacuo. Subsequently, the dried powder (0.050 g, 0.093 mmol) was dissolved in dry methanol (2.5 ml). One drop of 15% HCl was added to this solution which was agitated to cause mixing. 4-(Benzo­furan-2-carbonyl)-5-(4-tert-butyl­phenyl)-3-hy­droxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one hydro­chloride salt, (II), precipitated out of the solution and was isolated as an off-white powder (yield 0.0716 mmol, 0.039 g, 77%), while colourless crystals of the title salt, (I), crystallized out of the methano­lic solution as a by-product (<5% yield).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in idealized positions and were allowed to ride on their parent atoms, with C—H = 0.97 Å, N—H = 0.89 Å and O—H = 0.82 Å, and with Uiso(H) = 1.5Ueq(C,O) for primary ammonium and hy­droxy groups, and 1.2Ueq(C) otherwise.

Results and discussion top

The asymmetric unit of salt (I) consists of one 4-(3-aza­niumyl­propyl)­morpholin-4-ium dication, doubly protonated at atoms N1 and N2, counter-balanced by two different anions, viz. a hydrogen oxalate anion and a chloride anion (Fig. 1). The morpholine ring assumes a low-energy chair conformation, with the aza­niumyl­propyl side chain in an anti­periplanar (anti or trans) conformation [the C5—C6—C7—N2 torsion angle is 173.04 (8)°]. All other bond lengths and angles in the 4-(3-aza­niumyl­propyl)­morpholin-4-ium dication fall within expected ranges. Typical variations in the C—O bond lengths can be observed for the hydrogen oxalate anion; whereas the short bond distances of the charged carboxyl­ate end C8—O2 and C8—O3 [1.2474 (12) and 1.2571 (14) Å, respectively] indicates a delocalization of charge across both C—O bonds, the longer bond length observed for C9—O5 [1.3113 (14) Å] and the short length for C9—O4 [1.2150 (13) Å] is consistent with a carb­oxy­lic acid group containing distinct CO and C—OH bonds.

Fig. 2 shows the crystal packing along the crystallographic b axis in the form of layers. Hydrogen oxalate anions are sandwiched by the 3-(morpholin-4-yl)propan-1-aminium cations, which are in turn separated by the chloride anions, as viewed in the ac plane. The sandwiched hydrogen oxalate anions inter­act through a number of different hydrogen bonds, as shown in Fig. 3. The individual sandwich layers are connected through Couloumbic inter­actions involving the chloride anions.

The extensive network of inter­molecular inter­actions displayed in the structure of compound (I) can be described by a combination of graph-set symbols (Bernstein et al., 1995). Atom H8C is a triple donor to O1iii, O3iv and O4iv, with the H8C···O4iv distance shorter than the corresponding H8C···O3iv distance (see Table 2 for hydrogen-bond geometry and symmetry codes; Fig. 3). This results in a cyclic R22(5) motif.

Atoms H8A and H8B link the cations in a head-to-head manner through Cl1, resulting in chains that spiral down the crystallographic b axis (Fig 4). Furthermore, an additional head-to-tail pairing can be observed for the cations through the weak hydrogen bonding of H8C···O1iii. The H8C···O1iii inter­action connects the 4-(3-aza­niumyl­propyl)­morpholin-4-ium dications in a head-to-tail manner, forming C(9) chains that run diagonally along the ab face (Fig. 5a). Furthermore, the hydrogen oxalate anions are inter­connected via O—H···O hydrogen bonds, forming head-to-tail C(5) chains along the crystallographic b axis (Fig. 5b). Additional inter­molecular C—H···Cl inter­actions formed between H3A and the chloride counter-ion result in chains that spiral down the crystallographic b axis (Fig. 4). Furthermore, atom O2 is involved in inter­actions with N1—H1 and H6A, resulting in a ring denoted R21(6), while three additional hydrogen bonds (N—H1···O2, O5—H5···O3i and C3—H3B···.O2i) result in a third ring, denoted R33(12) in graph-set notation (Fig. 3). Due to the fact that atom O5 is a double donor to H3B and H1, several smaller rings can be identified that are contained within ring R33(13). These include R33(9) formed by N—H1···O5, O5—H5···O3i and O2i···C3—H3B; R22(8) formed by N—H1···O2 and O5···C3—H3B; and R21(5) formed by N—H1···O5 and O5···C3—H3B, as well as R12(5) formed by (N)H1···O2 and O5···(N)H1 and lastly R23(6) formed by H3B···O5, O5—H5···O3i and O2i···H3B. The C—H···O, O—H···O and N—H···O hydrogen-bond distances vary between 1.73 and 2.60 Å, while the N—H···Cl and C—H···Cl inter­action distances vary between 2.27 and 2.71 Å. All inter­actions in the structure are shorter than the sum of the van der Waals radii of the inter­acting atoms, where r(O) + r(H) = 2.72 Å and r(Cl) + r(H) = 3.00 Å, respectively (Mantina et al. 2009). In addition, the hydrogen-bond angles range between 133 and 172°, with the exception of N1—H1···O5 [123 (2)°], N2—H8C···O1iii (117°) and the nonclassical C3—H3B···O5 (114°). Most of the inter­actions observed in the structure therefore correspond well to what is considered strong hydrogen bonding, thereby contributing to the stability of the structure.

Residual electron density is found on a twofold axis near atoms H6B (2.33 Å), H2A (2.38 Å) and Cl1 (2.89 Å). Probing of the electron density showed it to be well positioned to be a water molecule with possible H2O—H hydrogen bonding to H6B and H2A, as well as showing a possible O—H···Cl short inter­action. Refining of the residual electron density as an O atom, however, indicated that the occupancy would be very low as well as having huge uncertainty in the H-atom placement due to lack of electron density. Taking into account the low occupancy of any atom placed in this position, it is plausible that the residual electron density is an artefact in the data.

Related literature top

For related literature, see: Bernstein et al. (1995); Brammer et al. (2002); Gein et al. (2007); Gouzerh & Proust (1998); Hill & Prossner-McCartha (1995); Huang et al. (2009); Mantina et al. (2009); Mizuno & Misomo (1998); Proust et al. (1993); You et al. (2006); Zhou & Yu (2012); Zhuang et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006), DIAMOND (Brandenburg, 2006) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the crystallographic b axis.
[Figure 3] Fig. 3. N—H···O, O—H···O and C—H···O hydrogen bonding, and N—H···Cl and C—H···Cl intermolecular interactions (dashed lines) between the 4-(3-azaniumylpropyl)morpholin-4-ium dication, hydrogen oxalate anions and the chloride anions of (I). [Please indicate symmetry codes for repeat labels]
[Figure 4] Fig. 4. N—H···Cl and C—H···Cl intermolecular interactions (dashed lines) between the chloride anions and 4-(3-azaniumylpropyl)morpholin-4-ium dications arranged in a head-to-head fashion, spiralling down the crystallographic b axis.
[Figure 5] Fig. 5. (a) C(9) chains formed diagonally along the crystallographic ab plane through intermolecular N—H···O interactions (dashed lines) between the 4-(3-azaniumylpropyl)morpholin-4-ium dications and (b) C(5) chains formed along the crystallographic b axis through intermolecular O—H···O interactions (dashed lines) between the hydrogen oxalate anions. In both chains, the molecules are arranged in a head-to-tail fashion.
4-(3-Azaniumylpropyl)morpholin-4-ium chloride hydrogen oxalate top
Crystal data top
C7H18N2O2+·C2HO4·ClF(000) = 1152
Mr = 270.71Dx = 1.430 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9809 reflections
a = 18.949 (5) Åθ = 2.4–28.3°
b = 5.685 (5) ŵ = 0.32 mm1
c = 24.783 (5) ÅT = 100 K
β = 109.575 (5)°Block, colourless
V = 2515 (2) Å30.32 × 0.24 × 0.14 mm
Z = 8
Data collection top
Bruker APEX-II CCD
diffractometer
2954 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.033
Graphite monochromatorθmax = 28.4°, θmin = 1.7°
ϕ and ω scansh = 2525
46562 measured reflectionsk = 77
3150 independent reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0441P)2 + 2.538P]
where P = (Fo2 + 2Fc2)/3
3150 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 1.26 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C7H18N2O2+·C2HO4·ClV = 2515 (2) Å3
Mr = 270.71Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.949 (5) ŵ = 0.32 mm1
b = 5.685 (5) ÅT = 100 K
c = 24.783 (5) Å0.32 × 0.24 × 0.14 mm
β = 109.575 (5)°
Data collection top
Bruker APEX-II CCD
diffractometer
2954 reflections with I > 2σ(I)
46562 measured reflectionsRint = 0.033
3150 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.03Δρmax = 1.26 e Å3
3150 reflectionsΔρmin = 0.23 e Å3
154 parameters
Special details top

Experimental. Crystals of [C7H18N2O]2+·C2HO4-·Cl-, (I), were grown by slow evaporation from a saturated methanolic solution of 4-(benzofuran-2-carbonyl)-5- (4-(tert-butyl)phenyl)-3-hydroxy-1-(3-morpholinopropyl)-1H-pyrrol-2(5H)-one (II), acidified with hydrochloric acid.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Crystal evaluation and data collection were performed on a Bruker APEXII CCD diffractometer with Mo Kα (λ = 0.71069 Å) radiation and a diffractometer-to-crystal distance of 4.00 cm, at the Department of Chemistry, Auckland Park campus of the University of Johannesburg, South Africa. The initial cell matrix was obtained from two series of scans at different starting angles. Each series consisted of 12 frames collected at intervals of 0.5° in a 6° range with the exposure time of 10 s per frame. The reflections were successfully indexed by an automated indexing routine built in the APEXII program suite (APEX2 and SAINT; Bruker, 2012). The final cell constants were calculated from a set of 3150 strong reflections from the actual data collection.

The data were collected by using the full-sphere data collection routine to survey the reciprocal space to the extent of a full sphere to a resolution of 0.75 Å. Data were harvested by collecting frames at intervals of 0.5° scans in ω and ϕ, with exposure times of 20 s per frame. These highly redundant data sets were corrected for Lorentz and polarization effects. The absorption correction was based on fitting a function to the empirical transmission surface as sampled by multiple equivalent measurements (SADABS; Bruker, 2012).

The systematic absences in the diffraction data were uniquely consistent for the space group C2/c that yielded chemically reasonable and computationally stable refinement results. A successful solution by direct methods (SHELXS97; Sheldrick, 2008) provided all non-H atoms from the E-map. All non-H atoms were refined with anisotropic displacement parameters.

The final least-squares refinement of parameters against data resulted in residuals R (based on F2 for I 2σ) and wR (based on F2 for all data) values unique to the crystal.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.06713 (6)0.09471 (18)0.61326 (5)0.0148 (2)
H1A0.10970.19020.63470.018*
H1B0.03840.18260.57950.018*
C20.01853 (6)0.04815 (18)0.65010 (4)0.01290 (19)
H2A0.00080.19580.66040.015*
H2B0.04760.03190.68500.015*
C30.01715 (6)0.32481 (17)0.60042 (4)0.01205 (19)
H3A0.01210.40990.63450.014*
H3B0.05830.42430.57850.014*
C40.03162 (6)0.26306 (18)0.56479 (5)0.0143 (2)
H4A0.00170.18120.53040.017*
H4B0.05040.40650.55330.017*
C50.10022 (6)0.15209 (18)0.64870 (4)0.01321 (19)
H5A0.13680.26760.62770.016*
H5B0.07280.21740.68600.016*
C60.14042 (6)0.07162 (19)0.65617 (5)0.0148 (2)
H6A0.15700.15850.62040.018*
H6B0.10610.17070.68510.018*
C70.20762 (6)0.01054 (18)0.67407 (5)0.0142 (2)
H7A0.19070.05870.71200.017*
H7B0.23900.10330.64760.017*
N10.04685 (5)0.10181 (15)0.61690 (4)0.01050 (17)
H10.07250.02360.58420.013*
N20.25144 (5)0.22804 (16)0.67412 (4)0.01376 (18)
H8A0.29080.19260.68450.021*
H8B0.22260.33130.69870.021*
H8C0.26720.29020.63910.021*
O10.09326 (4)0.11814 (13)0.59603 (3)0.01537 (16)
C80.16604 (6)0.21555 (17)0.48876 (4)0.01075 (18)
C90.19432 (6)0.03209 (17)0.46434 (4)0.01088 (19)
O20.11121 (4)0.22588 (13)0.53391 (3)0.01368 (15)
O30.20129 (4)0.38517 (13)0.45938 (3)0.01467 (16)
O40.24188 (4)0.05627 (13)0.41753 (3)0.01467 (16)
O50.16082 (4)0.20390 (13)0.49869 (3)0.01502 (16)
H50.17750.33030.48400.023*
Cl10.367263 (14)0.01834 (4)0.729512 (10)0.01563 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0145 (5)0.0119 (4)0.0192 (5)0.0021 (4)0.0073 (4)0.0019 (4)
C20.0116 (4)0.0125 (4)0.0138 (5)0.0029 (3)0.0032 (4)0.0025 (4)
C30.0128 (4)0.0093 (4)0.0140 (4)0.0003 (3)0.0044 (4)0.0005 (3)
C40.0151 (5)0.0131 (4)0.0156 (5)0.0013 (4)0.0061 (4)0.0021 (4)
C50.0124 (4)0.0140 (4)0.0150 (5)0.0011 (4)0.0068 (4)0.0008 (4)
C60.0141 (5)0.0142 (5)0.0178 (5)0.0002 (4)0.0076 (4)0.0003 (4)
C70.0137 (5)0.0139 (5)0.0166 (5)0.0012 (4)0.0070 (4)0.0006 (4)
N10.0099 (4)0.0101 (4)0.0110 (4)0.0004 (3)0.0029 (3)0.0000 (3)
N20.0121 (4)0.0160 (4)0.0129 (4)0.0013 (3)0.0039 (3)0.0006 (3)
O10.0125 (3)0.0139 (3)0.0210 (4)0.0012 (3)0.0071 (3)0.0027 (3)
C80.0117 (4)0.0098 (4)0.0115 (4)0.0011 (3)0.0049 (3)0.0007 (3)
C90.0106 (4)0.0099 (4)0.0125 (4)0.0006 (3)0.0044 (3)0.0001 (3)
O20.0144 (3)0.0116 (3)0.0122 (3)0.0010 (3)0.0007 (3)0.0003 (3)
O30.0162 (4)0.0101 (3)0.0149 (3)0.0007 (3)0.0013 (3)0.0006 (3)
O40.0151 (4)0.0128 (3)0.0132 (3)0.0018 (3)0.0009 (3)0.0000 (3)
O50.0178 (4)0.0079 (3)0.0152 (4)0.0007 (3)0.0000 (3)0.0003 (3)
Cl10.01616 (14)0.01693 (13)0.01260 (13)0.00007 (8)0.00323 (10)0.00131 (8)
Geometric parameters (Å, º) top
C1—O11.4260 (15)C5—H5B0.9700
C1—C21.5215 (15)C6—C71.5224 (15)
C1—H1A0.9700C6—H6A0.9700
C1—H1B0.9700C6—H6B0.9700
C2—N11.5018 (13)C7—N21.4897 (16)
C2—H2A0.9700C7—H7A0.9700
C2—H2B0.9700C7—H7B0.9700
C3—N11.4983 (16)N1—H10.9100
C3—C41.5177 (14)N2—H8A0.8900
C3—H3A0.9700N2—H8B0.8900
C3—H3B0.9700N2—H8C0.8900
C4—O11.4270 (13)C8—O21.2474 (12)
C4—H4A0.9700C8—O31.2570 (14)
C4—H4B0.9700C8—C91.5550 (18)
C5—N11.5030 (13)C9—O41.2150 (13)
C5—C61.5253 (17)C9—O51.3114 (14)
C5—H5A0.9700O5—H50.8200
O1—C1—C2111.88 (9)C7—C6—H6A109.6
O1—C1—H1A109.2C5—C6—H6A109.6
C2—C1—H1A109.2C7—C6—H6B109.6
O1—C1—H1B109.2C5—C6—H6B109.6
C2—C1—H1B109.2H6A—C6—H6B108.1
H1A—C1—H1B107.9N2—C7—C6109.38 (9)
N1—C2—C1108.91 (8)N2—C7—H7A109.8
N1—C2—H2A109.9C6—C7—H7A109.8
C1—C2—H2A109.9N2—C7—H7B109.8
N1—C2—H2B109.9C6—C7—H7B109.8
C1—C2—H2B109.9H7A—C7—H7B108.2
H2A—C2—H2B108.3C3—N1—C2108.26 (8)
N1—C3—C4108.69 (9)C3—N1—C5111.23 (8)
N1—C3—H3A110.0C2—N1—C5113.41 (8)
C4—C3—H3A110.0C3—N1—H1107.9
N1—C3—H3B110.0C2—N1—H1107.9
C4—C3—H3B110.0C5—N1—H1107.9
H3A—C3—H3B108.3C7—N2—H8A109.5
O1—C4—C3111.42 (9)C7—N2—H8B109.5
O1—C4—H4A109.3H8A—N2—H8B109.5
C3—C4—H4A109.3C7—N2—H8C109.5
O1—C4—H4B109.3H8A—N2—H8C109.5
C3—C4—H4B109.3H8B—N2—H8C109.5
H4A—C4—H4B108.0C1—O1—C4110.43 (9)
N1—C5—C6110.86 (9)O2—C8—O3127.20 (10)
N1—C5—H5A109.5O2—C8—C9117.81 (9)
C6—C5—H5A109.5O3—C8—C9114.97 (10)
N1—C5—H5B109.5O4—C9—O5125.34 (10)
C6—C5—H5B109.5O4—C9—C8121.51 (9)
H5A—C5—H5B108.1O5—C9—C8113.14 (9)
C7—C6—C5110.22 (9)C9—O5—H5109.5
O1—C1—C2—N158.32 (11)C6—C5—N1—C3170.13 (8)
N1—C3—C4—O160.11 (11)C6—C5—N1—C267.56 (11)
N1—C5—C6—C7165.38 (8)C2—C1—O1—C458.45 (11)
C5—C6—C7—N2173.05 (8)C3—C4—O1—C159.29 (11)
C4—C3—N1—C258.92 (10)O2—C8—C9—O4171.81 (10)
C4—C3—N1—C5175.84 (8)O3—C8—C9—O47.03 (14)
C1—C2—N1—C358.00 (10)O2—C8—C9—O57.05 (13)
C1—C2—N1—C5178.06 (8)O3—C8—C9—O5174.11 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.911.872.7400 (16)160
N1—H1···O50.912.443.0568 (12)125
N2—H8A···Cl10.892.323.1846 (11)162
N2—H8B···Cl1i0.892.273.1445 (13)166
N2—H8C···O4ii0.892.112.9093 (16)149
N2—H8C···O3ii0.892.523.1901 (13)133
N2—H8C···O1iii0.892.553.0583 (13)117
O5—H5···O3iv0.821.732.548 (2)172
C3—H3A···Cl1v0.972.713.6067 (12)154
C3—H3B···O2iv0.972.333.233 (2)154
C3—H3B···O50.972.583.1050 (14)114
C5—H5A···O4vi0.972.413.3323 (16)158
C6—H6A···O20.972.603.3733 (15)137
C7—H7B···O4vi0.972.473.359 (2)153
Symmetry codes: (i) x1/2, y1/2, z+3/2; (ii) x1/2, y1/2, z+1; (iii) x1/2, y1/2, z; (iv) x, y+1, z; (v) x+1/2, y+1/2, z; (vi) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC7H18N2O2+·C2HO4·Cl
Mr270.71
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)18.949 (5), 5.685 (5), 24.783 (5)
β (°) 109.575 (5)
V3)2515 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.32 × 0.24 × 0.14
Data collection
DiffractometerBruker APEX-II CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
46562, 3150, 2954
Rint0.033
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.080, 1.03
No. of reflections3150
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.26, 0.23

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006), DIAMOND (Brandenburg, 2006) and ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.911.872.7400 (16)159.8
N1—H1···O50.912.443.0568 (12)125.1
N2—H8A···Cl10.892.323.1846 (11)162.4
N2—H8B···Cl1i0.892.273.1445 (13)166.4
N2—H8C···O4ii0.892.112.9093 (16)149.0
N2—H8C···O3ii0.892.523.1901 (13)132.9
N2—H8C···O1iii0.892.553.0583 (13)116.8
O5—H5···O3iv0.821.732.548 (2)171.9
C3—H3A···Cl1v0.972.713.6067 (12)154.4
C3—H3B···O2iv0.972.333.233 (2)154.2
C3—H3B···O50.972.583.1050 (14)113.8
C5—H5A···O4vi0.972.413.3323 (16)158.3
C6—H6A···O20.972.603.3733 (15)137.2
C7—H7B···O4vi0.972.473.359 (2)152.6
Symmetry codes: (i) x1/2, y1/2, z+3/2; (ii) x1/2, y1/2, z+1; (iii) x1/2, y1/2, z; (iv) x, y+1, z; (v) x+1/2, y+1/2, z; (vi) x1/2, y+1/2, z+1.
 

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